Time and Time Again
by stargazer21
Summary: The first time was sweet, with her being the good girl and he being the bad boy. The second time was electric, an exploration of things that were repressed years before. The third time, well that, that was just painful.
1. Default Chapter

**TITLE:** Time and Time Again

**RATING:** R

**PAIRING:** Rory/Jess

**SUMMARY:** okay this is complicated so pay attention....Jess left Rory like he did on the show except in season three except she never saw him again and moved on.....years later in Rory's junior year at Yale they run into each other in New York and have a brief affair......more years later Rory is a successful writer in a group the press labeled "Fishermen's Club" because of an anectodote of the group when they were students at Yale. They eventually all write novels and become this famous literary group...... Jess is recruited by one of Rory's friends to join them in New York where they are all living so they can publish his stuff, which they all agree is good. Rory and Jess haven't seen each other since the affair and they find themselves falling for each other yet again.

**AUTHOR'S NOTE:** I know that this is somewhat confusing, but stay with me because I worked and thought hard not to make this you basic future fic where Rory and Jess meet up years later, Jess is a writer and Rory has a man. Also, be sure to review please. I can't improve if you guys don't give me feed back. And......check out my other stories.

_FLASHBACK......._

_Rory was lying on her stomach watching old music videos in her white tank top and baby blue panties on the rumpled sheets of the bed. The mid afternoon light poured into the large windows that revealed the East Village in all its glory and hypocrisies. The bohemian history with the yuppie inhabitants. The old buildings with the Starbucks in it. _

_The hotel room was small, but cheap, and Rory had tried her best to keep it as clean as possible. She would giggle every few minutes at the huge hair of the rockers singing "Talk Dirty to Me," and the overalls of the men begging "Come on Eileen."_

_Jess was leaning against the headboard in his boxers watching her and enjoying his perspective. He found Rory quite amusing and lovely. He had tried to focus on Faulkner, but was distracted by her light giggle floating toward him and reminding him of her presence. He threw the book on the floor with a thud gaining Rory's attention purposefully._

_He moved to lie next to her while Rory kept her eyes focused on the screen, of Run DMC singing with Areosmith. He took the remote which was lying next to her and switched the screen off._

"_What do you think you're doing?"_

_Jess began kissing her freckled shoulder as he said, "As if you didn't know." Rory smiled at this and watched him kiss her shoulder curiously. Jess moved her hair long dark hair out of the way as he kissed her neck, lightly pulling down the strap of her tank top in the process. Rory felt nerves moving all over her body, swirling and spinning slowly. She sighed softly and Jess mumbled in her neck, "Roll over." And she complied helplessly, her silky hair falling off the front side of the bed in folds._

_Jess kissed Rory feverishly on the lips while pulling her small tank top out of the way so he could enjoy what he loved so much more. He placed his hand, palm down, on her small smooth porcelain stomach and kept it very still, pulling his face away from Rory's so he could watch, before moving his hand back and forth over the skin above the blue band sending chills in every direction in Rory's body. _

_He smiled, loving the painful anticipation. _

"_Sometimes I wonder why I even bother to put clothes on at all," she said breathlessly. Jess looked at her and smirked before pulling her underwear off and tossing them on the floor. Rory's breath quickened and she closed her eyes as he put one hand over her right breast and played with her soft skin. Although she tried not to, she moaned loudly._

"_I would love it if you never wore any clothes." Jess whispered before leaning down and kissing Rory, moving his hands to either side of her face while their bodies pressed against each other. _

_Chest against chest. _

_Skin against skin. _

_Rory pumped her hips into Jess' showing him she was ready, causing him to make a strangled sound. In one motion his boxers were off and they joined both crying out. Rory closed her eyes and put both her hands on his back, squeezing the skin with her fingers. She felt a warmth spread through her body in waves, crashing into the shore in a steady rhythm rendering her completely at its mercy. _

_It was not the wild frenzied bucking and yelling of the night before, but it was slow, soft and deliberate. _

_Jess lips stayed on her neck while Rory's soft touch moved lightly and painfully all over his backside. Jess' left hand cupped Rory's face and she bit the side of his hand. Their eyes met and Jess struggled to keep his gaze on her delicious baby blues. He felt himself drowning, shaking, too vulnerable and intense. She threw her head back and Jess knew it would be soon. He moved faster, focusing on the friction between them and the noises coming from Rory's lips that he thought the loveliest sound in the world. _

_Afterwards they held each other and when they woke the room was dark and their stomachs growled. "What do you feel like doing tonight?" she asked as his head rested on her chest tenderly._

"_More of what we did earlier."_

"_Besides that." She smiled in the darkness._

"_Food."_

"_Then?"_

"_Let's see a movie, an old one."_

"_Okay, but sadly that means I will have to put on clothes."_

"_That does make me a bit sad." _

_END OF FLASHBACK....._

"Rory?"

"Hmm?"

"What's it like where you are?" Ethan looked at her smiling and placed an affectionate hand on her arm that was holding her drink.

"Oh, sorry. I just dazed out." Rory smiled and shook her head. She looked around the party at everyone else having a good time, smiling and laughing. She looked back at her boyfriend, dressed well in a dark gray suit and crisp white shirt. Ethan always dressed well. It was part of his upbringing, he always said.

"I can see that." Ethan took a sip out of his wine and waited for Rory to say something. When she didn't, he said, "Is something wrong?"

"No of course not. I am just exhausted with everything." Rory looked around the room again. At the thirty or so impeccably dressed people, some famous, most not. She was tired of the same scenes, the same literary crowd, the same ass kissers, the same pretentious conversations, the same jokes, the same thing almost every night. Rory felt a wave of hostility wash over her, and she told her self to behave.

"I know, me too, but after tonight we are done. We can go back to New York, back to real culture and bask in our gloriousness." Rory took a sip out of her wine as Ethan spoke, knowing that he almost always said something similar to her at every party they went to. What he was really saying was "Stop complaining. Enjoy this." Rory saw, and had seen many times, how well Ethan did at these literary book parties, how charming he could be, and how much he enjoyed it. Though she did not.

Rory felt uncomfortable with her new fame. She had never intended to be a novelist. At Yale, she wrote one short story under pressure of her friends who were all writers, titled "The Illusionist," and it had been well received and published in their creative writing journal on campus. People came up to her quoting lines back to her. Rory wrote a few more, and they seemed to be popular. Then after graduation while she was working at a horrible little newspaper, Emily, Ethan, and Chris were writing novels and she ended up expanding a short story. Just to see, Rory told herself at the time.

It was all so unintentional.

Not only did the thing get good reviews. But it sold! At first Rory assumed that was due to everyone in Stars Hollow buying three copies, but it kept selling. And journalists, a profession she once aspired to, called her and wanted interviews with the famous group of friends. They were famous! They had money! They had fans!

And they even had a name "Fishermen's Club."

It was in the basement of their dormitory that they became good friends discussing food, sex, and literature. Rory had joined because she thought Chris and Emily were cool. And she told herself sophomore year would be different. She would meet more people and expand her horizons. Boy did she ever.

When Emily told her counselor she wanted to be a writer, the counselor replied stiffly "You will have more success as a fishermen." And then they had their name. Just like that. Everyone started calling themselves fishermen.

"You will return to New York and bask in your gloriousness. I on the other hand will be going to Stars Hollow the antithesis of real culture." Rory smiled, for him, and put her glass on a nearby table.

"I forgot." Ethan finished his drink and set it on the table too. He put both his hands on Rory's hips, able to feel her form perfectly under the thin material of her green dress.

"I've been talking about this for weeks."

"I'm sorry." Ethan's green eyes stared back at Rory, and she couldn't help but wonder what color eyes their kids would have. Green or blue? "I just want you with me. I am going to be lonely in the city without you." He leaned forward and kissed her softly on the lips.

"It's only for a week." She reached out and ran a hand through his sandy blond hair.

"Don't go."

"I can't not go. It's my mother."

Later after an hour of mingling and two more glasses or red wine, Rory stood outside on the balcony staring at the ocean, it was too beautiful and she hated that, because she hated California and she wanted to keep that hate.

The house was modern, high ceilings and metal furniture, and every room seem to be white. It didn't really feel like a home, even though Rory had met the couple who owned the house. She slipped her feet out of her shoes which had caused her some pain over the course of the night, and stood in bare feet on the stone floor wiggling her toes freely.

"Can I join you?"

"Sure Emily." Rory smiled at her friend. Emily walked toward her from the other side of the long balcony, her short blonde hair and stretchy white dress catching the moonlight wonderfully. Sometimes, like at that moment, Rory felt insecure next to her friend with her beautiful blonde hair and wonderful figure. Rory couldn't help feel that she had the body of a twelve year old boy.

"I am so ready to go home," Emily said with a dramatic roll of the eyes. She was always dramatic, and her novel reflected that. It was about a family with an abusive father and pill popping mother. Almost every page had a fight or a sex scene or a breakdown. Oprah had read aloud from it on her show, loving it. It was called Undone and Unbound.

"Me too."

"I mean this book tour has been exhausting. One thing right after another. It has been great that all of us can be together on it, and that the publicity has been good. But I just need my space." She looked out to the ocean, at the silver streaks in the water. "You know what I mean?"

"I know."

"I guess it is different for you since you have Ethan. This has been some romantic adventure for you guys."

"Let me tell you, nothing says romance like literary parties and book signings."

"I meant hotel bedrooms and room service." The girls laughed hard and Rory realized that she was slightly drunk and that Emily was not. She stood a little straighter and griped the silver railing for support.

"Is Chris here yet?" Chris was their other great friend from Yale who the press had labeled a member of the "Fishermen's Club" and wrote a novel, Don't Look Down. Instead of going on the book tour with everyone else he instead moved to LA for the summer, living with his brother. They had seen his short stories published in Harper's, New York Times Magazine, and Vanity Fair. When they talked to him on the phone, Chris said he was waiting for his next "big idea." Rory, Ethan, and Emily hadn't seen him in four months.

"I talked to him on my cell; he's running late."

"He is always late," Rory said looking in on the party. She was glad to be out on the balcony.

"But it is comforting that some things never change, isn't it?" Rory didn't get a chance to answer.

"Hey, my favorite girls!" Chris appeared and they hurried to him. Rory, Emily and Chris talked and laughed on the balcony. Jokes were made about his new tan, scruffy look, and longer hair. He asked how they liked LA and how the party was going. Rory smiled at the familiar banter and how Chris was still the funny guy she met in her physics class sophomore year. When Chris finished his story about his latest romance with an aspiring actress he looked at Rory and smiled.

"What?"

"I got a surprise for you." Chris smiled mischievously at Rory and she smiled back unsure and embarrassed at the sudden attention.

"A present?"

"No. Not a present."

"What then?"

"Come here." He took her by the hand and led her back into the party past crowds of people, past important journalists from the LA times and photographers for Rolling Stone. Rory laughed a little out of nervousness and giddiness with Chris and Emily. It was fun having Chris back, she thought as he opened the door into one of the bedrooms.

Rory's smile left her and her breath caught in her throat when her baby blues met the familiar brown eyes that paralyzed her so long ago. She swallowed thickly looking briefly at Chris and Ethan and Emily and then back to Jess, all looking at her.

"Rory, I believe you know Jess." Chris was smiling, proud of the situation he had construed.

"Oh my God." Rory realized that she was making the situation more awkward than necessary. She searched her brain for more rational thoughts. Something to say. Questions to ask him or anyone. But she couldn't. She stood there dumbly, staring at Jess who stared back at her. Waiting for her response.

"Hi," he said simply. Jess had always been able to keep cool, she thought. She was always the dramatic one, the emotional one. She smiled and walked toward him and gave him a hug.

It was a clumsy and awkward embrace. Rory had rushed toward him quite suddenly and Jess wasn't expecting to be hugged at all. The feel of their bodies against each other set off a wave of chills and Rory's blood moved faster and faster, then froze. She pulled away and took a step back, very much aware her boyfriend and two friends were staring at them curiously.

"Oh my God." And she laughed to hide her embarrassment and nervousness. Rory willed herself to look at Ethan and gave him a smile, which she knew Jess would see, then back to Jess.

"You said that already," Jess said.


	2. 2

**AUTHOR'S NOTE: **Thank you for all that reviewed, and everyone else that didn't feel free to do so this time around.

"You said that already," Jess said.

"I know. I am just shocked to see you." Rory smiled again. And Jess could tell it was out of nervousness. She looked around the room at her friends and brushed a strand of hair nervously behind her ear. Jess stood stoically as the scene unfolded before him. He felt that the less he said, the better.

"So you're surprised," Chris said looking at Rory.

"Very. I mean, it's been forever," she said incredulously looking at Jess. And he wondered what she saw. An older wiser Jess? A good looking Jess? A not so attractive ex-boyfriend? A mistake?

"Since high school," Jess said quickly holding Rory's gaze. The blue eyes still have their power, he thought.

When he had first told Chris that he knew Rory Gilmore, Jess didn't want to appear like some asshole bragging he fucked this girl once. He couldn't bring himself to tell Chris the truth. Instead he revealed the partial truth. The easier part. That Jess had lived in Stars Hollow, with his uncle Luke, and had briefly dated Rory.

"Yeah, since high school," Rory said looking at Jess. He saw the emotions running across Rory's face. There was a secret, a lie. Something to keep hidden. And it was theirs.

"Jess is like my best friend here," Chris said patting Jess on the back, who was uncomfortable with the gesture.

His eyes remained on Rory. She looked wonderful. He couldn't deny that. The green dress hung well on her small frame and was a good color on her. Her hair was long again. And Jess liked that. He could tell, the way she was standing, the way her arms were crossed, her shifting eyes, that she was uncomfortable. Because of him.

His eyes drifted to the light freckles on her shoulders. He remembered kissing those freckles over and over again and breathing in the skin.

"Really," Rory said shooting a look at Jess.

"The only decent person in this god forsaken place." Chris rolled his eyes.

"I thought you liked it here," Ethan said.

And Jess looked at him, fully regarding Ethan. His sandy well cut hair, white button down shirt, the nice suit. But Jess had seen images of Ethan long before that in magazines and papers, and once on television. Jess had read Ethan's book as well, twice. It was called Boy Wonder. Jess hated it.

"I do. I like the girls, but sometimes it's like talking to my six year old niece," Chris answered.

"That's dirty," Emily said smiling.

Jess looked at Emily who, he then realized, was smiling at him. He supposed that she was beautiful. Blonde hair, tan skin, big boobs. But since living in California he had fucked a dozen in that mold, more. And they all formed one blonde blur in his mind. He looked back to Rory looking at Ethan, and he hated that.

"Rory, Jess is a writer," Chris said.

"You are," Rory said softly. Jess raised his eye brows and tried to say something clever and witty that would stop her dead in her tracks. But he couldn't think of anything.

"He's pretty good too." Chris also looked at Ethan and Emily when he spoke. Jess knew that this was part of something, him being let into their silly group. He needed to play the role of the new guy.

"What have you written?" Rory asked Jess directly. For a second, his throat seemed to go dry. They hadn't spoken in so long. Just the idea of them having a normal conversation was strange, especially with her boyfriend standing right next to her.

"Some short stories." Jess tried to keep his voice casual and non-committal.

"And a novel. Gabe has read it and he's going to publish it," Chris interjected.

"Gabe's publishing it!" Rory exclaimed. Jess saw how shocked she was. He realized it must be a bit much for her. They hadn't seen each other in three years, and now her good friends were praising him and publishing his work.

Gabe Hernandez was the editor and publisher of all the "Fishermen's Club" novels. Gabe had not attended Yale with everyone, but was a cousin of Emily. The success of "Fishermen's Club" had made him quite a rich man, and a bit of a celebrity in the literary world. He was the one to discover the talents and he wielded some power over the group. Jess had met him once, and he could tell Gabe was someone who believed in good literature and money, and he was in the business of both.

"Our little group is growing, expanding, getting bigger," Ethan said.

"Wow. Congratulations, Jess," Rory said shaking her head, as if she couldn't quite believe it. Her shiny dark hair moved in soft waves. Jess noticed it was the first time she said his name. He loved the way it rolled off her tongue in that soft way. Almost as if she was sighing in bed or something.

"Thanks," was all he could reply.

_FLASHBACK............................_

_Jess woke to an empty bed. He sat up and looked around the empty room. Her bags were still there. Her things, her clothes still on the floor and hung over the chair. Jess sighed in relief. Then he noticed the bathroom light coming from out of the cracks of the door. _

_Jess lied back down and waited. And waited. He strained his ears but couldn't hear anything. The clock read 3:26. At 3:40 he would get up and see if something was wrong. Jess tried to gather his thoughts and focus them elsewhere, but couldn't. The minutes went by agonizingly slow. He looked over again, for what seemed like the millionth time, and read 3:39. Close enough, he thought._

_He got up and slid a pair of boxers on, and walked to the bathroom. Three light knocks._

"_Rory?" Jess put the side of his head against the door._

"_Yeah?" Her voice seemed casual. _

"_Are you okay?" _

"_Fine."_

"_Can I come in?"_

"_Sure." Jess opened the door and saw her lying in the bathtub, soaking in the water. She was completely exposed and made no effort to hide herself from him. Jess couldn't help but look her wet and shiny form over. _

"_What are you doing?" One of her legs was bent and sticking out of the soapy water, while the other laid flat in the bottom of the tub. Her hand rested on her thigh while the other was bent, Rory's elbow on the side of the tub. _

"_Solving the world's energy crisis." _

"_It's four o'clock in the morning."_

"_I couldn't sleep." She shrugged and Jess watched the shine on her skin shift with her movements._

"_Do you do this often?"_

"_Bathe?"_

"_At this hour."_

"_Never."_

"_But when you do, do you usually lie just like this?" Jess stepped closer to the tub until he was right next to her. And he knelt to look at her face to face. He liked thinking of her like this. Of her lying so sweetly in the water waiting for him to open his eyes and come in._

"_I guess." Her hair was also wet, and slicked back on her head some of it floating on the surface of the water around her shoulders. _

"_You know you are driving me crazy, don't you?" Jess lightly ran his hand up and down her wet arm, his eyes transfixed on his movements. He told himself to hold onto that moment, to remember Rory like she is now for ever. He tried to memorize the details. _

"_I know you're scared to admit you're crazy about me." Rory put her hand on top of Jess, her wet fingers mingling with his. _

"_I'm not scared. I have loved you since I was seventeen." Jess leaned forward and put his lips to Rory's. The kiss was soft and wet, like Rory, Jess thought. His tongue slid naturally into her mouth and met hers. Jess moved closer and closer and let go of Rory, except for his mouth, and put his hands on the edge of the tub. He smiled into the kiss, and stepped into the bathtub. _

"_You are crazy!" Rory squealed, delighted. _

_END OF FLASHBACK............._

"Small world, huh?" Chris took a bite out of the French toast he was eating. He sat on the opposite side of the plastic lime green booth from Jess. When the party was winding down Chris and Jess decided to get some real food and come there. They had, of course, invited everyone else to come but they had declined. Rory and Ethan were tired, so they said, and Emily wanted to write something down which was in her head.

Jess had not failed to notice how quickly Rory said "No, I am too tired." How quickly her polite smile vanished when she met Jess' eyes. He also noticed when they were sitting down, having decided to mingle one last time before leaving, how Ethan's hand rested naturally on Rory's thigh.

"Apparently so," Jess said before eating some of his scrambled eggs.

They were sitting in the diner they always went in after a night of partying of drinking. It was open 24 hours a day and served great burgers. Jess looked around and saw mostly other people his age, a few teenagers. All seemed drunk and laughing stupidly to him. It was all familiar territory for Jess, as well as Chris who sat across from him.

"So, what did you think of everyone?"

"They were cool."

"Good."

"Rory seemed surprised."

"Sorry about that." Chris looked back to Jess, away from the group of teenage girls who had just walked into the diner, giggling in very short skirts. Jess noticed that Chris was easily distracted.

"You said you told her I was going to be there."

"I almost did." Chris took a drink from his water before asking, "Was it weird for you?"

"As much as would be expected from seeing someone from high school." Jess down played the reunion.

"Good cause when you move to New York you will probably see a lot of her."

"I told you I hadn't decided on anything." Jess shook his head.

"If Gabe is publishing your book then you have to be there!" Chris rolled his eyes. This was a familiar argument.

"I don't have to do anything. It is not part of my contract that I take up residence across the country. Away from my friends, my family, my entire life." Jess was reluctant to move to New York. He had a lot of history there.

That, and he knew that some might see him as a stalker.

Her friend in her little group helped him publish his book by her publisher. And if he moved there, and saw her often, how could he keep his sanity? It was better to stay away. At least he had told him self that for so long.

"You don't really have any friends, not good ones anyway. You are not even close with your family and your life here is dead. Your new life is in New York." Jess knew that Chris really was motivated by good. He told himself that because he was getting incredibly irritated by him. Especially after the stunt with Rory.

"According to you."

"God, can't you just take my advice for once without the Jess Mariano commentary."

"Nope, it comes with the whole package."

"Listen, everything important to publishing your book is in New York. The parties, the press, the people. Don't you want it to sell?"

"That's the difference between me and your group you guys started," Jess leaned forward putting his elbows on the plastic table in between them. "I just want the thing to get good reviews. Not even a lot. Just one and I will be happy. I am perfectly content on not being the next John Grisham."

"I am not talking John Grisham, I am talking James Baldwin."

"No, you are talking Jonathan Frazen."

"Jess, just tell me that you will think about it."

"I'll think about it."

**AUTHOR'S NOTE:** This is moving slowly. I know. I hate fics where it goes too fast, so you guys have the flashbacks to keep you satisfied. Also, this fic deals a lot with the literary world of writers, publishers, press, book readings and editing. I think a lot of fics have Jess as a writer but nothing of what it is actually like for a writer living in New York. Although my premise is a bit cliché, this is where I feel mine stands out. If you feel this works, or doesn't, review and tell me about it.


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